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Chester was made in CAS, in his young adult years so he doesn't have memory of this age. If not made in CAS, this is when he would have began dating Kaitlyn.
Chester and Kaitlyn married. They adopted a dog named Mallory. They adopted another dog named Travis. Kaitlyn became pregnant with their first child. She later suffered a miscarriage (my game glitched). Kaitlyn eventually became pregnant again. She gave birth to a baby girl named Haley. Chester and Kaitlyn divorced not long after. After the divorce Chester became dating Lucy Ferne. They have a son named Cayden. Chester and Lucy have decided against marriage.